A coastal landscape with a beach, ocean waves, and a sunset sky.

Find Hotels with a Pool in Wainscott, NY

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Wainscott Hotels with a Pool

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Wainscott hotels with a pool

A swimming pool with two lounge chairs and a green umbrella.
A beach with pebbles and sand, a sunset, and a calm sea.
A wooden outdoor seating area with a sofa and a table, surrounded by gravel and greenery, with a house in the background.
A wooden building with a white window and a balcony.

1. The Sagaponack

The Sagaponack
Wainscott
  • Take a summer dip in the seasonal outdoor pool with loungers for relaxing in the Hamptons sun.
$236 nightly
$269 total
Nov 4 - Nov 5
Total with taxes and fees
The Sagaponack
Outdoor pool
Living area
Room
Terrace/patio

2. East Hampton House Resort

East Hampton House Resort
East Hampton North
  • Seasonal outdoor pool creates a refreshing escape at this hotel, with tennis courts and gardens adding to the resort atmosphere.
$159 nightly
$181 total
Nov 2 - Nov 3
Total with taxes and fees
East Hampton House Resort
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.
A bathtub surrounded by candles and flower petals.
A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.
An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

3. A Room At The Beach

A Room At The Beach
Bridgehampton
  • Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
$296 nightly
$338 total
Oct 7 - Oct 8
Total with taxes and fees
A Room At The Beach
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A hotel lobby with a sofa, chairs, tables, and a large window.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

4. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
$219 nightly
$250 total
Nov 1 - Nov 2
Total with taxes and fees
Sag Harbor Inn
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.
A modern kitchen with a central island, pendant lights, and a view of the outdoors.
A living room with a fireplace, two sofas, a coffee table, and a chair.

5. Journey East Hampton

Journey East Hampton
East Hampton North
  • Seasonal poolside splendor at East Hampton hotel with complimentary bikes and garden views.
$257 nightly
$294 total
Oct 18 - Oct 19
Total with taxes and fees
Journey East Hampton
A house with a sloped roof, large windows, and a pathway leading to the entrance.
A wooden gate leading to a pathway surrounded by lush greenery and trees.
A covered porch with white railings, green cushioned chairs, hanging flower baskets, and pendant lights.
A cozy living room with a white sofa, a dining table with chairs, a chandelier, a potted plant, and framed pictures on the wall.

6. Mill House Inn

Mill House Inn
Pantigo Road Historic District
  • Soak in serene poolside moments at this charming Colonial B&B with a garden terrace for ultimate relaxation.
$411 nightly
$470 total
Oct 12 - Oct 13
Total with taxes and fees
Mill House Inn
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A bar area with shelves stocked with various bottles and glasses.
A modern hotel room with a bed, bedside table, and a view of the garden.
A large, white, two-story building with a covered porch and a bicycle parked in front.

7. Topping Rose House

Topping Rose House
Bridgehampton
  • Serene outdoor pool creates luxurious oasis in the Hamptons; perfect for unwinding after coastal adventures.
$607 nightly
$698 total
Oct 18 - Oct 19
Total with taxes and fees
Topping Rose House
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A spacious living room with a fireplace, comfortable seating, and large windows.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
$450 nightly
$515 total
Nov 2 - Nov 3
Total with taxes and fees
Faraway Sag Harbor
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

9. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
$143 nightly
$163 total
Oct 21 - Oct 22
Total with taxes and fees
The Bentley Hotel Southampton
A large indoor swimming pool with multiple lanes, safety signs, and a tiled wall with hexagonal patterns.
A coastal pathway with a wooden bridge leading to a green sports court.
A modern bathroom with a glass shower enclosure, a bathtub, and a wall-mounted faucet.
Two Adirondack chairs facing a beach with a clear view of the ocean.

10. Ocean Vista Resort

Ocean Vista Resort
Amagansett
  • Oceanside sanctuary provides splendid private beach access and indoor pool oasis.
$127 nightly
$145 total
Oct 20 - Oct 21
Total with taxes and fees
Ocean Vista Resort
View all properties

Choose what matters most at hotels with a pool in Wainscott

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Wainscott Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Great"
Linda 2-night trip
Posted 4 hours ago
Gurney's Montauk Resort & Seawater Spa
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"."
andrew 1-night trip
Posted 11 hours ago
Ocean Vista Resort
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Nice room close to beach"
Christina 2-night trip
Posted 12 hours ago
Ocean Resort Inn
The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"My only complaint would be i wish there was a Keurig machine in the room instead of an espresso machine. Would definitely stay there again."
Fred 2-night trip
Posted 15 hours ago
The Atlantic Hotel
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"Montauk Yacht Club was the perfect getaway for my boyfriend and I to celebrate our 3 year anniversary. Our room was spotless and had a great view of the water. We did mention to them ahead of time that it was our anniversary, thinking they might have some champagne or something waiting in the room for us, but they did not. Nonetheless, it was still a perfect stay. We played tennis and the courts were beautiful. The on-site restaurant was very yummy as well! I definitely recommend coming during the off season, as it is way less crowded in town and very relaxing."
Sarah 3-night trip
Posted 1 day ago
Montauk Yacht Club
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 2 days ago
Ocean Surf Resort
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Beachcomber was wonderful loved it"
elizabeth 3-night trip
Posted 6 days ago
Beachcomber Resort at Montauk

Frequently asked questions

How much does a hotel with outdoor pool in Wainscott cost?
Enjoy staying in a hotel in Wainscott with an outdoor pool. You can find a great deal from $145 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Wainscott with outdoor pool cabanas or loungers?
The Sagaponack is a charming 3-star hotel in Wainscott that offers a delightful outdoor pool experience. Guests rave about the inviting pool area, featuring comfortable sun loungers and shaded umbrellas, great for lounging on a sunny day. With a review rating of 8.8, visitors appreciate the hotel's friendly staff and the nice decor that adds to the overall appeal.Beyond the pool, The Sagaponack also provides complimentary toiletries and free WiFi, ensuring a convenient stay for families. Plus, self-parking is available at no additional cost, making it easy to explore the beautiful surroundings of Wainscott.
Is it cheaper to book flights and a Wainscott hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Wainscott for you.

Explore a world of travel with Expedia